(2-bromoethyl)(octadecyl)(2-hydroxyethyl)phosphate | 1609100-54-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: (2-bromoethyl)(octadecyl)(2-hydroxyethyl)phosphate
• 英文别名: 2-Bromoethyl 2-hydroxyethyl octadecyl phosphate；2-bromoethyl 2-hydroxyethyl octadecyl phosphate
• CAS: 1609100-54-0
• 化学式: C₂₂H₄₆BrO₅P
• 分子量: 501.482
• InChiKey: JZBGMVZHDIANDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.79
• 重原子数：
  29.0
• 可旋转键数：
  24.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2-bromoethyl)(octadecyl)(2-hydroxyethyl)phosphate 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 、 chlorotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 120.0h， 生成 2-((choline)(octadecyloxy)phosphoryloxy)ethoxyretinoate
  参考文献：
  名称：

  Novel cationic polyene glycol phospholipids as DNA transfer reagents—Lack of a structure–activity relationship due to uncontrolled self-assembling processes

  摘要：

  Cationic glycol phospholipids were synthesized introducing chromophoric, rigid polyenoic C-20:5 and C-30:9 chains next to saturated flexible alkyl chains of variable lengths C6-20:0. Surface properties and liposome formation of the amphiphilic compounds were determined, the properties of liposome/DNA complexes (lipoplexes) were established using three formulations (no co-lipid, DOPE as a co-lipid, or cholesterol as a co-lipid), and the microstructure of the best transfecting compounds inspected using small angle X-ray diffraction to explore details of the partially ordered structures of the systems that constitute the series. Transfection and cytotoxicity of the lipoplexes were evaluated by DNA delivery to Chinese hamster ovary (CHO-K1) cells using the cationic glycerol phospholipid 1,2-dioleoyl-sn-glycero-3-ethylphosphocholine (EPC) as a reference compound.The uncontrollable self-association of the molecules in water resulted in aggregates and liposomes of quite different sizes without a structure-property relationship. Likewise, adding DNA to the liposomes gave rise to unpredictable sized lipoplexes, which, again, transfected without a structure-activity relationship. Nevertheless, one compound among the novel lipids (C-30:9 chain paired with a C-20:0 chain) exhibited comparable transfection efficiency and toxicity to the control cationic lipid EPC. Thus, the presence of a rigid polyene chain in this best performing achiral glycol lipid did not have an influence on transfection compared with the chiral glycerolipid reference ethyl phosphocholine EPC with two flexible saturated C-14 chains. (C) 2014 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2014.04.006
• 作为产物：
  描述：

  硬脂醇 、 2-溴乙基二氯膦酸酯 、 乙二醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 以34%的产率得到(2-bromoethyl)(octadecyl)(2-hydroxyethyl)phosphate
  参考文献：
  名称：

  Novel cationic polyene glycol phospholipids as DNA transfer reagents—Lack of a structure–activity relationship due to uncontrolled self-assembling processes

  摘要：

  Cationic glycol phospholipids were synthesized introducing chromophoric, rigid polyenoic C-20:5 and C-30:9 chains next to saturated flexible alkyl chains of variable lengths C6-20:0. Surface properties and liposome formation of the amphiphilic compounds were determined, the properties of liposome/DNA complexes (lipoplexes) were established using three formulations (no co-lipid, DOPE as a co-lipid, or cholesterol as a co-lipid), and the microstructure of the best transfecting compounds inspected using small angle X-ray diffraction to explore details of the partially ordered structures of the systems that constitute the series. Transfection and cytotoxicity of the lipoplexes were evaluated by DNA delivery to Chinese hamster ovary (CHO-K1) cells using the cationic glycerol phospholipid 1,2-dioleoyl-sn-glycero-3-ethylphosphocholine (EPC) as a reference compound.The uncontrollable self-association of the molecules in water resulted in aggregates and liposomes of quite different sizes without a structure-property relationship. Likewise, adding DNA to the liposomes gave rise to unpredictable sized lipoplexes, which, again, transfected without a structure-activity relationship. Nevertheless, one compound among the novel lipids (C-30:9 chain paired with a C-20:0 chain) exhibited comparable transfection efficiency and toxicity to the control cationic lipid EPC. Thus, the presence of a rigid polyene chain in this best performing achiral glycol lipid did not have an influence on transfection compared with the chiral glycerolipid reference ethyl phosphocholine EPC with two flexible saturated C-14 chains. (C) 2014 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2014.04.006

文献信息

• [EN] NOVEL CATIONIC CAROTENOID-BASED LIPIDS FOR CELLULAR NUCLEIC ACID UPTAKE<br/>[FR] NOUVEAUX LIPIDES CATIONIQUES À BASE DE CAROTÉNOÏDE POUR LA CAPTURE CELLULAIRE D'ACIDE NUCLÉIQUE
  申请人：PUNGENTE MICHAEL D

  公开号：WO2014071072A2

  公开（公告）日：2014-05-08

  The synthesis and self-assembling properties of a model compound in a new class of cationic phospholipids with a highly unsaturated conjugated carotenoid fatty acid are described. In addition, the potential of this new lipid as a nucleic acid carrier was evaluated through lipoplex formulations employing 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) as helper lipid with and without the polycationic peptide, protamine, together with a plasmid DNA (pDNA). Lipoplexes composed of this novel unsaturated lipid exhibited pDNA binding and protection from DNase I degradation when formulated with protamine. Cellular uptake of the liposomes could be monitored by the visible color of the carotenoid moieties. The new cationic lipid gene delivery vector revealed comparable transfection efficiency to the commercial lipid, 1,2-dimyristoyl-sn-glycero-3-ethylphophocholine (EPC), in Chinese hamster ovary-K1 (CHO-K1) cells and performed equally to Lipofectamine 2000 when the formulation included protamine.